CN101454268B - 包含衍生自2-芳基-2-羟基乙酸的配体和二价或者三价金属阳离子的金属络合物及其用途 - Google Patents
包含衍生自2-芳基-2-羟基乙酸的配体和二价或者三价金属阳离子的金属络合物及其用途 Download PDFInfo
- Publication number
- CN101454268B CN101454268B CN2007800188697A CN200780018869A CN101454268B CN 101454268 B CN101454268 B CN 101454268B CN 2007800188697 A CN2007800188697 A CN 2007800188697A CN 200780018869 A CN200780018869 A CN 200780018869A CN 101454268 B CN101454268 B CN 101454268B
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- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229910052751 metal Inorganic materials 0.000 title claims abstract description 44
- 239000002184 metal Substances 0.000 title claims abstract description 44
- 150000001768 cations Chemical class 0.000 title claims abstract description 26
- 239000003446 ligand Substances 0.000 title abstract description 8
- 150000004696 coordination complex Chemical class 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims description 32
- 239000007864 aqueous solution Substances 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 21
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 claims description 12
- 239000000843 powder Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 150000001457 metallic cations Chemical class 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 208000027219 Deficiency disease Diseases 0.000 claims description 6
- 159000000000 sodium salts Chemical class 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- 125000002091 cationic group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000008346 aqueous phase Substances 0.000 abstract description 18
- 230000007812 deficiency Effects 0.000 abstract 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 64
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 239000000243 solution Substances 0.000 description 37
- 229910052742 iron Inorganic materials 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 241000196324 Embryophyta Species 0.000 description 17
- 230000007935 neutral effect Effects 0.000 description 16
- 238000000034 method Methods 0.000 description 15
- 150000002500 ions Chemical class 0.000 description 10
- 239000011777 magnesium Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- -1 alkali metal salt Chemical class 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 150000003818 basic metals Chemical class 0.000 description 4
- 150000004687 hexahydrates Chemical class 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- GTNWAKLEMPDSQC-UHFFFAOYSA-N 2-(5-chloro-2-hydroxyphenyl)-2-hydroxyacetic acid Chemical compound OC(=O)C(O)C1=CC(Cl)=CC=C1O GTNWAKLEMPDSQC-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 229910052728 basic metal Inorganic materials 0.000 description 3
- 229930002875 chlorophyll Natural products 0.000 description 3
- 235000019804 chlorophyll Nutrition 0.000 description 3
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 238000006862 quantum yield reaction Methods 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000000536 complexating effect Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 150000004698 iron complex Chemical class 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229910001038 basic metal oxide Inorganic materials 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000012272 crop production Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- PZZHMLOHNYWKIK-UHFFFAOYSA-N eddha Chemical compound C=1C=CC=C(O)C=1C(C(=O)O)NCCNC(C(O)=O)C1=CC=CC=C1O PZZHMLOHNYWKIK-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 235000012204 lemonade/lime carbonate Nutrition 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- MOOYVEVEDVVKGD-UHFFFAOYSA-N oxaldehydic acid;hydrate Chemical compound O.OC(=O)C=O MOOYVEVEDVVKGD-UHFFFAOYSA-N 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/418—Preparation of metal complexes containing carboxylic acid moieties
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Agronomy & Crop Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fertilizers (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0604679A FR2901553B1 (fr) | 2006-05-24 | 2006-05-24 | Complexes metalliques comprenant un ligand derive d'acide 2-aryl-2-hydroxyacetique et un cation metallique divalent ou trivalent, et leur utilisation |
| FR0604679 | 2006-05-24 | ||
| PCT/EP2007/054847 WO2007135109A1 (en) | 2006-05-24 | 2007-05-21 | Metal complexes comprising a ligand derived from 2-aryl-2-hydroxyacetic acid and a divalent or trivalent metal cation, and their use |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210034650.9A Division CN102603368B (zh) | 2006-05-24 | 2007-05-21 | 包含衍生自2-芳基-2-羟基乙酸的配体和二价或者三价金属阳离子的金属络合物及其用途 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101454268A CN101454268A (zh) | 2009-06-10 |
| CN101454268B true CN101454268B (zh) | 2012-07-11 |
Family
ID=37762551
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2007800188697A Active CN101454268B (zh) | 2006-05-24 | 2007-05-21 | 包含衍生自2-芳基-2-羟基乙酸的配体和二价或者三价金属阳离子的金属络合物及其用途 |
| CN201210034650.9A Active CN102603368B (zh) | 2006-05-24 | 2007-05-21 | 包含衍生自2-芳基-2-羟基乙酸的配体和二价或者三价金属阳离子的金属络合物及其用途 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210034650.9A Active CN102603368B (zh) | 2006-05-24 | 2007-05-21 | 包含衍生自2-芳基-2-羟基乙酸的配体和二价或者三价金属阳离子的金属络合物及其用途 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8372176B2 (he) |
| EP (1) | EP2029515B1 (he) |
| CN (2) | CN101454268B (he) |
| BR (1) | BRPI0712260B1 (he) |
| ES (1) | ES2568931T3 (he) |
| FR (1) | FR2901553B1 (he) |
| IL (1) | IL195399A (he) |
| PL (1) | PL2029515T3 (he) |
| WO (1) | WO2007135109A1 (he) |
| ZA (1) | ZA200808874B (he) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019121228A1 (en) * | 2017-12-22 | 2019-06-27 | Basf Se | Aqueous composition comprising 2-(dimethyl-1h-pyrazole-1-yl) succinic acid and at least one metal hydroxide |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3960536A (en) * | 1973-09-25 | 1976-06-01 | Pepro, Societe Pour Le Developpement Et La Vente De Specialites Chimiques | Antichlorosis compositions for plants |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5745134A (en) * | 1980-08-04 | 1982-03-13 | Nippon Kayaku Co Ltd | Isolation of p-hydroxymandelic acid |
| FR2638740B1 (fr) * | 1988-11-08 | 1991-07-12 | Hoechst France | Nouveau procede de fabrication industrielle du parahydroxymandelate de sodium |
| FR2739618B1 (fr) * | 1995-10-04 | 1998-01-02 | Hoechst France | Complexe orthohydroxymandelate de sodium-phenol-eau, procede de preparation et utilisation pour isolement de l'orthohydroxymandelate de sodium |
| FR2759618B1 (fr) | 1997-02-20 | 1999-05-07 | Euro Stic | Dispositif et procede de decollage d'etiquettes de leur support |
| NL1010090C2 (nl) * | 1998-09-15 | 2000-03-17 | Gerard Kessels Sociedad Anonim | Werkwijze voor de bereiding van 2- en 4-hydroxyamandelzuur. |
-
2006
- 2006-05-24 FR FR0604679A patent/FR2901553B1/fr not_active Expired - Fee Related
-
2007
- 2007-05-21 WO PCT/EP2007/054847 patent/WO2007135109A1/en active Application Filing
- 2007-05-21 ES ES07729291.0T patent/ES2568931T3/es active Active
- 2007-05-21 EP EP07729291.0A patent/EP2029515B1/en active Active
- 2007-05-21 CN CN2007800188697A patent/CN101454268B/zh active Active
- 2007-05-21 BR BRPI0712260-8A patent/BRPI0712260B1/pt active IP Right Grant
- 2007-05-21 CN CN201210034650.9A patent/CN102603368B/zh active Active
- 2007-05-21 US US12/301,806 patent/US8372176B2/en active Active
- 2007-05-21 PL PL07729291T patent/PL2029515T3/pl unknown
-
2008
- 2008-10-16 ZA ZA2008/08874A patent/ZA200808874B/en unknown
- 2008-11-20 IL IL195399A patent/IL195399A/he active IP Right Grant
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3960536A (en) * | 1973-09-25 | 1976-06-01 | Pepro, Societe Pour Le Developpement Et La Vente De Specialites Chimiques | Antichlorosis compositions for plants |
Also Published As
| Publication number | Publication date |
|---|---|
| IL195399A (he) | 2016-10-31 |
| CN102603368A (zh) | 2012-07-25 |
| EP2029515A1 (en) | 2009-03-04 |
| FR2901553B1 (fr) | 2011-08-26 |
| WO2007135109A1 (en) | 2007-11-29 |
| US20100288004A1 (en) | 2010-11-18 |
| CN102603368B (zh) | 2014-06-25 |
| BRPI0712260A2 (pt) | 2012-01-17 |
| PL2029515T3 (pl) | 2016-08-31 |
| FR2901553A1 (fr) | 2007-11-30 |
| ZA200808874B (en) | 2009-12-30 |
| BRPI0712260B1 (pt) | 2018-06-26 |
| EP2029515B1 (en) | 2016-03-09 |
| IL195399A0 (en) | 2009-08-03 |
| CN101454268A (zh) | 2009-06-10 |
| US8372176B2 (en) | 2013-02-12 |
| ES2568931T3 (es) | 2016-05-05 |
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| C06 | Publication | ||
| PB01 | Publication | ||
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